A modified vancomycin binding pocket (D-O-E ring) incorporating an alpha -hydroxy-beta -amino acid at the AA4 position is designed and synthesized. Some of these compds. display potent bioactivities against both sensitive- and resistant-strains (8 micro g/mL against VREF). Both the lipidated aminoglucose and the structure of the 16-membered macrocycle are found to be important for the anti-VRE activities. The polyamine appendage at the C-terminal, on the other hand, improved the activity against vancomycin-sensitive strains. [on SciFinder (R)]
Title
Identification of synthetic compounds active against VRE: the role of the lipidated aminoglucose and the structure of glycopeptide binding pocket
Published in
Bioorganic & Medicinal Chemistry Letters
Volume
15
Issue
20
Pages
4594-4599
Date
2005
ISSN
0960-894X
Note
CAN 143:440728
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
1404-90-6DP (Vancomycin); 868749-33-1P; 868749-34-2P; 868749-35-3P; 868749-36-4P; 868749-37-5P; 868749-38-6P; 868749-40-0P; 868749-42-2P; 868749-49-9P; 868749-50-2P; 868749-93-3P; 868749-94-4P Role: PAC (Pharmacological activity), SPN (Synthetic preparation), THU (Therapeutic use), BIOL (Biological study), PREP (Preparation), USES (Uses) (role of lipidated aminoglucose and structure of glycopeptide binding pocket in synthetic compds. active against VRE); 847505-78-6; 868684-96-2; 868684-97-3; 868685-00-1; 868685-01-2 Role: RCT (Reactant), RACT (Reactant or reagent) (role of lipidated aminoglucose and structure of glycopeptide binding pocket in synthetic compds. active against VRE); 868684-98-4P; 868684-99-5P; 868749-27-3P; 868749-28-4P; 868749-29-5P; 868749-30-8P; 868749-31-9P; 868749-32-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (role of lipidated aminoglucose and structure of glycopeptide binding pocket in synthetic compds. active against VRE)
Record creation date
2010-11-25
